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Aluminium lithium hydride → 1,1-Dimethylethyl N-[(1R)-2-[1,1′-biphenyl]-4-yl-1-formylethyl]carbamate

HRID 1052906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1052906
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([C:22](=[O:27])NCOC)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH:22]=[O:27])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)([CH3:2])([CH3:4])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 67969567HCID 67969567, Verbindung

Produkt 1

HCID 103142381,1-Dimethylethyl N-[(1R)-2-[1,1′-biphenyl]-4-yl-1-formylethyl]carbamateAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-2.5 °C

Versuchsvorschrift

[(R)-2-Biphenyl-4-yl-1-(methoxymethylcarbamoyl)ethyl]carbamic acid t-butyl ester (7.5 g, 19.5 mmol, 1.0 eq.) was combined with THF (distilled) (100 mL) under nitrogen. Lithium aluminum hydride (750 mg, 19.8 mmol, 1.0 eq.) was added to the resulting stirred solution in several batches at −5-0° C. over a period of 30 minutes. The resulting solution was stirred for 30 minutes at −5-0° C. The reaction was then quenched by the addition of a solution of KHSO4 (6.6 g) in water (35 mL). The resulting solution was combined with a 1N HCl (75 mL) solution, and stirred for five minutes. EtOAc (100 mL) was added and the resulting solution was extracted with EtOAc (3×100 mL) and the organic layers were combined to yield the title compound (6.3 g) as a yellow oil.

Aufarbeitung

  1. stirringThe resulting solution was stirred for 30 minutes at −5-0° C
  2. customThe reaction was then quenched by the addition of a solution of KHSO4 (6.6 g) in water (35 mL)
  3. stirringstirred for five minutes
  4. additionEtOAc (100 mL) was added
  5. extractionthe resulting solution was extracted with EtOAc (3×100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-12cef897452848beb5812236ea188cb4
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388145B2

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